


Took Me Long Enough

by CeliPuff



Category: Supernatural
Genre: Alternate Universe - High School, Best Friends, Bisexual Dean Winchester, Castiel is Not Innocent (Supernatural), Castiel is That Bitch, Castiel/Dean Winchester First Kiss, Dean Winchester Has a Crush on Castiel, Dean Winchester Has a Sexuality Crisis, Eventual Smut, F/F, F/M, Gay For You, High School Castiel/Dean Winchester, M/M, Openly Gay Castiel (Supernatural), POV Dean Winchester, Sam Winchester Ships Castiel/Dean Winchester, falling for your best friend, high school seniors
Language: English
Status: Completed
Published: 2019-10-24
Updated: 2019-11-11
Packaged: 2021-01-02 13:48:04
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 12
Words: 18,011
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21162647
Author URL: https://archiveofourown.org/users/CeliPuff/pseuds/CeliPuff
Summary: Alright, so you know how in movies the friendzoned BFF always gets the girl in the end? Well what if the girl is a dude and you’re also a dude? Do the same rules apply? Or will this clusterfuck end with me losing my best friend?





	1. Chapter 1

Cas is… well, awesome. We’ve been friends since the sixth grade and it's hard to even remember who my best friend was before him. Benny and Charlie are great, don’t get me wrong, but what I have with Cas is next level. I don’t even have to say what I'm thinking, he always knows.

Cas is gay. I mean, he tried the bi thing and after some very awkward sexcapades with his _ex_ girlfriend this past summer, he realized and accepted his homosexuality. Ever since then, his confidence has almost tripled.

The skinny, shy kid with messy hair I met has transformed into this tall, confident man, complete with the messy hair, that is suddenly sexy to pretty much every teenager in this den of hormones we call high school.

Don’t get me started on his fucking eyes. The shade of blue they are should be illegal and it doesn’t help that the dude is pretty intense. You know, eye contact, give you all of my attention kind of intense. This guy won’t even pull out his phone if someone is talking to him, and demands the same respect or he’ll snatch your phone and fuck with your contact names.

One time he changed my mom’s name to my girlfriend Lisa’s name, the thorough asshole even changed the photo. Let’s just say, I was grounded the next week for what I texted her.

I should say _ex girlfriend_ Lisa, we broke up a few weeks ago. Once Cas broke up with Meg we started spending a lot more time together and Lisa started acting different, constantly wanting me to spend time with her and less with Cas. The breakup was amicable but today was still going to be awkward, maybe we’ll get lucky and have no classes together. As if, Lawrence High isn’t _that_ big.

Cas and I made a pact, Senior year _will_ be different. We won't be tied down by some chicks _or dudes_ this year. We both turn eighteen in a few months and already started planning for the apartment we’re going to rent together. Sam wasn’t happy I planned on moving out soon but it had to happen one day.

Sam’s a freshmen this year and the _only_ person to know about my feelings for Cas. I know I _could_ talk to my friends about it but… come on, this was _Cas!_ I couldn’t bring myself to tell anyone and Sam only knew because of a drunken confession after a house party two weeks ago. By the way, I will never drink tequila again. Mistakes were made.

When I think back to the day I realized I loved my best friend, it feels more like damn chick flick then my actual life.

We were at the beach, _typical._ Summer just started, we ditched our girlfriends, jumped in my beautiful ‘67 Impala and drove until we hit water. We somehow decided it was a good idea to day drink. Just us. That was when Cas told me he was gay. Yeah, I already knew he liked dudes, he always had and never tried to deny it but this conversation was different.

“Dean, I’m gay.” Cas said, staring into my eyes as usual.

“Uh okay Cas. Didn’t we all know this? I mean your first kiss was that Nick kid in the sixth grade.” I really didn’t see how this was news.

“No, I mean _gay._ Like, my dick hates my girlfriend and won’t even give her the time of day, _gay._” Cas laughed at himself. “She tried so hard this weekend, god it would have been embarrassing if I gave a fuck.” He ran a hand through his hair, “I admitted that I picture a dude when she sucks me off so I could come. Was that mean?”

I couldn’t hold back my laugh, “Fuck Cas, that’s brutal!” I always loved how the guy said what he felt and never held any punches. “Never change, Cas.”

“Fuck.” We laughed together for awhile before he continued, “Yeah, I think we broke up.” He shrugged. “It was bound to happen one day, at least all of my high school memories won't be me tied to some girl I don’t actually like. I’m retiring from vagina, Dean.”

Dude made a point. “Damn, all our high school memories _are_ of us tied to some girl. First it was Cassie and April, not that those lasted long and now Lisa and Meg. We need to spread our wings Cas.” That was the moment I decided I would break up with Lisa.

“Spread _our_ wings? And what of Lisa?” Cas had a knowing smile.

“I think I’m going to break up with her, I mean, I’ve wanted to for a while actually. And I can’t let you have all the damn fun this senior year, right?” Cas’ smile was contagious.

“Alright, Dean.” He held out his hand, “No relationships this year. Deal?”

I shook his hand with a nod, “Deal.”

We drank some more before I got the courage to ask. “So Cas, how did you know you liked dudes?”

Cas’ head tilt in confusion, I hated when he did that. He always looked so damn... cute. “Uh, well when I was seven Anna and I had a crush on the same guy from… never mind, I refuse to name the boy band. Stop laughing assbutt.”

His blush made it worse, “Please Cas, please name the boy band!”

“Fuck off, moving on. I just always knew Dean. I knew girls were pretty too but it never held the same merit. I dated girls because I thought it was what I was _supposed_ to do. You know? I don’t know how else to explain it.” He turned his body towards me on the bench, “How did you know you liked girls?”

Good question. “I don’t know, I guess I can see why you struggle to explain it. You just kinda know.” Or did I?

Cas stared at me uncomfortably long, eyes squinting before he spoke up again. “Are you straight Dean?”

No way he didn’t feel my entire body tense at that question. Who the _fuck_ says exactly what the they are thinking? Oh yeah, fucking Cas. “As far as I know.” Real fucking smooth.

We didn’t get very deep after that, he let it go and I wasn’t complaining. Cas did get a little too drunk and made some drunken confessions of his own. He told me how the day we met at school was the day he knew for a fact that he liked boys and how he had a crush on me most of sixth grade. He also said that when he kissed Nick behind the lunchroom he pretended it was me. He doesn’t remember telling me these things, but how could _I_ forget.

When I met Cas, I remember specifically thinking about how beautiful his eyes were and wanting to run a hand through his messy hair. I remember wishing I could hold his hand more than once. When he told me he kissed a boy, I remember feeling jealous. Jealous of Nick but also jealous that Cas was comfortable enough in himself to go for it and talk about it like it wasn’t a big deal.

I thought about how my dad would flip shit of he thought one of his sons were gay. I gave Cas all the support I would want if I ever had the courage to admit my feelings out loud and we have been inseparable since. I watched him try out for both teams, knowing deep down that he preferred dicks. His stories about his time with dudes were always more enthusiastic.

Meg knew what she was getting into but she insisted she could turn him straight when instead she _turned_ him fully gay. I wish I could have seen her face.

I had to give Cas a piggyback ride to Baby since his intoxicated ass kept stopping to try and build sand castles for bees, which of course made him pretend I was his own personal horse. Almost tossed him on his ass when he said _giddy up._ When we finally made it to the car, I laid Cas in the backseat and he fell asleep in seconds. I remember staring down at him, the way his mouth hung slightly open as he snored softly, curling himself into the leather seat, made me suddenly want nothing more than to kiss his beautiful soft plump lips. Not like he would remember right? I leaned in with my last bit of courage just as he turned towards me and whispered my name. I jumped so high I slammed my head into the roof which knocked me out of my daze. What the fuck was I thinking?

At least my moment of gay panic was alone, I slammed the car door and almost made a run for it. A run to where? Who the _fuck_ knows. I just knew I couldn’t look at Cas right then. It took almost an hour for me to fight off the damn panic attack and join Cas in the car to sleep. The next morning, it was as if nothing happened. For him at least.

Breaking up with Lisa was much easier than I thought it would be, seeing as all I could think about was Cas. When I finally broke it off, we had been kissing and for a brief moment her eyes were blue. When I looked down again and her eyes were brown I felt completely detached. She wasn’t what I wanted anymore.

So, anyway, here we are now. Senior year, fresh start. No chicks to tie us down and I’m completely in love with my best friend. _Sonofabitch!_


	2. Chapter 2

“Come on Sammy! You don’t want to be late on your first day of high school!” 

Sam came running out a few moments later, long brown hair flowing behind him like a friggen hair commercial. He slammed the car door, “You mean late to get Cas?”

“Shut up bitch. You should have cut your hair before the new year, you look like a Hansen brother.” 

I heard him whisper “jerk” under his breath but ignored it. 

When we pulled up to Cas’ house I noticed Sam wasn’t moving. “Get in the back freshmen, seniors get shotgun.” 

“Is Cas your boyfriend yet?” The little shit had the nerve. 

I’m sure my face was as red as a tomato and Cas would walk out any second, “What the hell Sam!” 

“Look when he’s your boyfriend, I’ll jump in the back but until then. I get shotgun, I’m in high school now too. Cas won’t even care Dean.” 

Just as I was about to argue Cas came strolling out. He was wearing some dark blue jeans, a tight fitted black Star Wars t shirt and some all black vans. His hair was a mess as usual and I couldn’t help but think how cute he looked. 

He climbed into the backseat, no complaints, and tossed his backpack to the side, completely distracted by his phone. “Hello Dean, Sam.” He said without looking up. 

“Oh, so it’s ok for _you_ to text when you talk to people but no one else can?” I had to punch Sam in the arm for the face he made at me.

“Apologies Dean.” Cas dramatically set his phone to the side, locking his intense blue eyes on mine in the rearview mirror. “How are you today?”

“Shut up Cas.” Fucking smartass. “Who are you texting anyway?” 

What the fuck was that smile? “A guy I met this weekend.” He said with a shrug and turned to look out the window.

I noticed Sam frown and look down in my peripheral. Whatever, I don’t need sympathy. I don’t care if Cas is sleeping around, good for him. I plan on doing the same shit anyway. “A guy at the beach? I thought that was a family reunion, you’re disgusting Cas.” 

Cas laughed at that and fucked up my hair. Dick. “Funny, I didn’t know you knew jokes, tell more.” Still a dick. 

Once we got to school, Sammy ran off to find his nerd crew and Cas and I chilled by baby for a bit. Neither of us wanting to see our ex girlfriends. “Have you and Meg talked at all?” 

“Nope. Don’t plan on it, I mean I don’t hate her but she isn’t very fond of me at the moment. The only reason she isn’t spreading rumors about our sex life is because she “turned me” gay.” Cas and his air quotes. “Thankfully it’s just as embarrassing for her. Have you talked to Lisa?” 

“Not really. She texted me she missed me last night but I didn’t respond.”

“You didn’t respond? Dick move Winchester.”

I just shrugged, “What is there to say Cas? I’m just not into it anymore.”

“No, good for you Dean. I didn’t really like her if I’m being honest.”

“You don’t like any of the girls I date Cas.”

“Because you always date bitches. And you don’t like anyone I date either.”

“_I_ date bitches?? And Meg was…” Cas laughed, exactly no argument. “So tell me about this guy?” 

Cas shrugged his shoulders, “We had sex.” 

“You met this weekend and already had sex?” Stupid question.

Cas’ face was a mix of shock and confused, “Really?” He rolled his eyes. “I can name a _few_ one night stands you’ve had Dean, don’t preach.” Narrowing his eyes before asking, “Or are you jealous?” 

I won’t say how many octaves my voice rose, “Jealous of what? Why would I be jealous some rando bent by best friend over in the sand?”

Cas laughed way louder than necessary, “Okay, first, _I_ bend _them_ over, haven’t met a man worthy enough to be their receiver… _yet._ Second, I was simply meaning the fact that I got laid this weekend and you didn’t. But now I’d like to discuss why you went that route.” 

“Ok whatever, don’t you have a class to get to, _Romeo?_” Cas smiled but didn’t push. Asshat.

What the fuck did Cas mean _yet?_ Jealous? Yeah right. Dean Winchester doesn’t do jealous. 

Who was it though? 

If my morning wasn’t thrown off enough, I had first period with Lisa _and_ Meg. No Cas, no Benny or Charlie, no backup. The bitches just had to sit by me too.

“So have you fucked my Clarence yet Deano?” Meg asked with a sneer. 

“What!? Why the fuck would you think that?” Play it cool man.

“Touchy? At least Castiel was honest with why we broke up, maybe your girl here deserves the same.” Hate this bitch.

“Fuck off Meg, you don’t know our story, since when are you two friends anyway?” Lisa has hardly looked at me. “What does any of this have to do with Cas?” Why did I ask.

Meg laughed at me of course, “You know you have your own ringtone _and_ text tone on Cas’ phone? No one else does. And he has it that way so he never misses your call. Even if we’re in the middle of a conversation, and you know Cas. Now why would he fuck with his moral compass if he wasn’t in love with you? I didn’t even have my own ringtone and I was blowing the guy, _most of the time_.” She rolled her eyes and continued, “And everyone can see you love him too, just be honest, have you fucked yet?” 

The teacher told everyone to be quiet at the perfect fucking time. Fuck. 

About a minute later Charlie came sprinting into the room. “I’m sorry! I overslept. I’m here.” She panted, leaning on the teacher’s desk. When  
She spotted me she took the seat behind me since the bitches took the seats next to me. 

“Way to go Charles. I didn’t think I had anyone in this class. What game did you stay up late playing?” Always some game.

“Zip it, handmaiden, I refuse to answer that.” She poked my head with her pencil and I was suddenly glad she was late and missed that awkward ass conversation with Meg.

I spent the rest of the class not listening to shit the teacher said, I couldn't even tell you what class it was. Why did she say everyone can see I love him? And why did Lisa look like she agreed?

Once class ended, Charlie and I made it out the door only to be cornered by Lisa and Meg again, great. “I forgot how many gays you hang out with Dean, hey there Charlie.” 

Charlie looked taken aback, “Yeah but I’m the coolest gay.” She retorted. 

“Dean doesn’t think so huh, Dean?” Meg and her stupid bitch face.

“You know what Meg, it’s not my fault Cas wants to fuck dudes and not you. It doesn’t matter how much you _look_ like a dude, you’re lacking the right parts, sweetheart.” I shoved past her before she could speak but her face was priceless. Man that felt good. 

Charlie caught up a moment later, “That was hilarious! Did you see her face?” Charlie didn’t push the bullshit Meg was saying and I’ll forever be grateful. Little did I know, she already knew.


	3. Chapter 3

By the middle of the semester, I had fallen _hard._ I hated seeing Cas flirt with other dudes and goddammit was he a flirt. He disappeared from almost every house party with someone. Not that I could talk, I went a little crazy trying to convince myself that girls were enough. They weren’t. I started picturing what Cas might have been doing with the dudes he disappeared with, even checked out some gay porn. Not going to lie, it looked hot. 

I never in a million years imagined myself being a bottom but after Cas said _he_ did the fucking I looked into it. Don’t ask why. The bottoms did seem to be enjoying themselves though. I guess once the top hits some dude version of a g spot it’s like next level orgasm and I would be lying if I said that didn’t sound nice. Cas said _yet_ as if he would switch if the right dude came along, maybe that dude is me?

Fuck, why am I even having these thoughts. Shit was way less complicated when I wasn’t trying to fuck my best friend. More than that, when I wasn’t trying to _date_ my best friend. With any chick I’ve been with it was all about sex, even with Lisa that was how it started. I only seriously dated her because it was an easy and consistent lay. It sounds fucked up but it’s the truth. 

With Cas it’s different, I love spending time with him, love talking to him, I just fucking love _him._ And with each passing day, it’s getting harder and harder to ignore it. I’ve even started openly flirting with the guy and the asshat flirts back like it’s nothing. Sometimes I’ll wink at him from across the classroom and he just winks back or blows a damn kiss, never missing a beat. He won’t hold my hand tho, that’s the _one_ thing he just _won’t_ do and after I thought about it, I realized that he never held Meg’s hand either. Couldn’t help but wonder why. 

Charlie and I were hanging out at the Roadhouse waiting on Cas and Benny to arrive when she finally brought it up, “What exactly are you waiting for Dean?” 

I looked up from my drink confused, “Uh, we’re both waiting. For our friends.” 

“Friends, yes. But what is it going to take for you and Cas to level up if you know what I mean?” She wiggled her eyebrows. 

Goddammit. “No, I don’t know what you mean Charlie.” I couldn’t bring myself to look her in the eyes. 

“Come on, Dean. Talk to me. I know how you both feel.” Both? How is it people see anything more, from _him_ especially. The guy flirts with everyone. 

“Look Charles. I’m just not ready for _this_ conversation okay?” Why attempt to lie? Charlie could always see right through me. It was annoying, but Charlie had always been the little sister I never wanted. Truth is, and don’t breathe a word of this to her, but I couldn’t make it through this whole jacked up situation without her.

“Okay Dean, but I’m here when you’re ready. Look they’re here.” She squeezed my hand to offer support before going back to her normal boisterous self. “What’s up bitches?” 

“Oh Charlie, I’d be your bitch any day. If only you had a dick.” Charlie rolled her eyes and ignored Cas, as always.

Benny spoke up shaking his head, “I don’t get it, what is it about dicks that made you completely switch teams Cas? How do you just give up chicks?” 

I was worried that my eyes were too wide so I closed them like a fucking weirdo. When I opened my eyes, Charlie was looking at me, Cas and Benny were laughing and looking at each other, thank god. 

Everyone awaited Cas’ response, it took him a second to realize we were all looking at him. “Oh, that was a real question? How graphic should I get?” He tilted his head at Benny, Cas’ eye contact making him look away.

“As graphic as you can.” Charlie said, baiting him with her eyes gleaming.

Cas sighed, obviously enjoying himself. “Well…” Cas leaned in, keeping his eyes on Benny just to fuck with him, I could see the regret writen on Benny’s face. “There’s something about getting a _man_ to bend to your will. You know that feeling you get when a chick moans your name? Have you ever found a woman’s g spot Benny? Think that times 100.” 

Benny tried to cut him off, “I think I got it brotha-”

“Oh, I’m not finished, have you ever made a woman squirt Benny? I have and again, it’s nothing compared to a man exploding at your fingertips as you pound into his prostate relentlessly.”

Benny stood up covering his ears with his hands, “Alright, alright Cher! Always painting too well of a picture Cas. Now if you’ll excuse me, I’ve gotta go see a man about a toilet.”

“Hopefully the _man_ doesn’t keep you too long, I could have you back out here in three minutes, tops.” Cas wiggled his eyebrows at Benny and laughed as he stalked away, “Wait Benny, top or bottom?” Benny didn’t even look back. “Too easy.” He turned to face me and I really wish he hadn’t, he had no idea the fucking hard on I had under that damn tabel. “Hello, Dean.” Him saying my name made it worse, so much worse.

“H-hey Cas, nice story.” I definitely didn’t stutter. You stuttered.

“Thank you, I hoped you would enjoy it.” What the _fuck_ does that mean. 

Enter stage Charlie, “That was great, I love how you make people squirm, Cas. Your story was actually _almost_ hot, needed more vagina.” She made a gagging noise. “You obviously haven’t made the right chicks squirt, there’s no going back.” She winked at Cas. I tried to pretend I wasn’t completely fucking clueless, chicks actually squirt? I thought that was fake and only in pornos. God they are so much gayer when they are together. 

Jo walked up with good timing, causing Charlie to have heart eyes, “You guys know what you want? Where did Benny go?” Sorry Charles, she’s more interested in Benny’s southern drawl. 

“He just needed to get away from another one of Cas’ inappropriate stories. He’s on his way back now.” Charlie pointed, not noticing Jo’s blush. 

“_Castiel,_ how is it you are always saying something inappropriate when I walk up?” Jo slapped his arm playfully. Almost looked like she was flirting with him. 

“You just have impeccable timing sweetheart.” Cas stared into her eyes, causing her blush to deepen. Definitely flirting. Wrong tree Jo, wrong fucking forest. They all turned to face me when I laughed. Which of course made me blush. Shit.

“I’m starving, can we get some food?” I hoped that would distract them enough from asking why I laughed. It worked.

But you can see my issue, Cas flirts with _everyone._ He’s literally gotten us free shit from old ladies because of his flirting, or maybe it’s some damn blue eyes voodoo shit.

We all ordered burgers, as usual. Benny was back to normal, he had nothing against gay people, he just didn’t want to picture it. I would say I could relate, but that just isn’t the case anymore and I’m honestly sick of hiding it. 

I want to be as confident as Cas is. He gives no fucks and it’s actually admirable. He _was_ turning into a slut though and that bothered me... even if it shouldn’t. I didn’t have the right to be bothered by it, in fact, it was down right hypocritical but goddammit _I_ wanted to be the one exploding in Cas’ hand… wait what? 

That came out wrong. Shit.


	4. Chapter 4

**Summary for the Chapter:**

> First kiss!

Homecoming was always fun, not for the football though, the partying. Alcohol is _everywhere,_ even if the school hires extra help to supervise. By halftime, most of us are hammered and hitting on someone. Charlie was under the bleachers with some chick from the other school, can’t wait to hear that story. Benny and Andrea started dating last month and are in that disgusting, inseparable puppy love stage, who knows where they were, probably giving their own kind of school spirit. That left Cas, me and too much booze. 

Meg and Lisa came by at one point, Meg asking if we fucked yet followed by Cas responding inappropriately with a, “Not yet, want to watch? We were thinking of recording it.” 

I probably would have blushed if I wasn’t at that, _fuck it_, stage of drunk. Plus, Meg’s disgusted face was priceless. As they walked away pouting, I was feeling adventurous, “Next time, let’s just make out to fuck with them.” Fuck did I really just say that. Play it cool, don’t look at Cas.

He still hasn’t said anything… guess I should stop staring at my shoes now. Fuck… fuck. 

Of course he’s staring at me, dude doesn’t miss anything. Stop _squinting_ your eyes at me asshat.

“Yeah?” Is all he says… yeah… Cool.

I took another drink, not that I needed it. He reached for the bottle and took one too before speaking again. “Let’s go for a walk.” 

“Alright, lead the way.” Cas stood up so I followed him. We walked around not saying much, the parking lot was much quieter and pretty dead, only a few couples making out in between cars. When we walked past some soccer mom van Cas pushed me into the side where no one could see us and stepped into my space.

“Could you do it Dean?” He asked in a much deeper voice than normal. “Could you kiss a man? Could you kiss… me?” He tilted his head at me in that challenging way of his, licking his lips. I couldn’t tell if he was fucking with me or if he was serious. 

Again, let me mention, I was drunk and apparently feeling bold so I leaned in, I was going for it until… he moved back. Shit.

Cas’ eyes widened and I realized the fucker was baiting me, _he_ wasn’t serious and was genuinely surprised _I_ was. 

“How drunk are you Dean?” He snatched the water bottle full of disgusting Wild Turkey from my hand. 

“I’m not drunk, you’re drunk.” Goddammit when will I learn to shut up.

“Dean I may be an asshole most of the time, but I’m not an asshole to you, I’m not going to kiss you while you’re intoxicated.” As if he _wasn’t_ just as intoxicated as me.

“Shut the fuck up and kiss me Cas.” Guess I’ll never learn. 

“Try again tomorrow.” Cas moved to walk away but I grabbed his arm, I had to know.

“Do you not want to?” Can I be any more friggen needy?

“Do I not want to? Are you fucking kidding me Dean? I’ve wanted to kiss you since I was twelve years old jackass. You know what, fuck it, i’m going to hell anyway.” 

Cas kissed me. 

Our _first_ kiss. Yeah, it was sloppy but it was everything I had thought about the last few months. His lips were bigger and softer than any chick I’ve _ever_ been with, my dick was fully awake the second I parted my lips and he stuck his tongue in my mouth. Cas was an aggressive kisser and god damn was it hot. 

He finally pulled away after about three minutes, or was it three hours? Either way, I wasn’t ready for it to end and based on his face, he wasn’t either. His blue eyes were blown with lust and when I looked down he definitely had a boner just like I did. It took a moment for him to speak. 

“Yeah, let’s see if you remember that in the morning.” He nodded his head towards the game and we slowly made our way back, smiling like fucking idiots.

We didn’t talk about. Our friends appeared one by one as the game went on, so we didn’t have much of an opportunity. I caught Cas looking at me more than one with an unreadable smirk. Almost felt like the dude was undressing me with his eyes. Not that I would complain. 

The road home was silent with Sam in the backseat. Yeah I know, drinking and driving, do me a favor will ya? Shut up. Anyways, other than a very embarrassing moment when Taylor Swift came on the radio that caused Cas and Sam to howl with laughter. Pretty sure my dickhead brother live streamed it but I’ll get him back later. I thought Cas had already forgotten our hot moment earlier. 

Until, he got out of the car. 

You know what that snarky bastard did as he closed the door? He winked! I wanted to punch his stupid perfect face and yet pull him in for another kiss at the same time. Instead, I put the car in drive and drove Sammy and I home.

I kind of avoided him that weekend, we texted like normal, never mentioning the kiss, but I stayed home. Charlie came barging into my room on Sunday to check on me. I tried to blame a hangover on why I stayed home on Saturday but she wasn’t buying it.

“Look, I haven’t pressured you but you should talk to _someone_. Every Frodo needs a Samwise. Talk to me dude. You’re like one step away from becoming a Nazghul?” I rolled my eyes at her for making sense, even if it was masked with a ton of nerd. I surprisingly _did_ want to talk about it. Here goes nothing.

“Cas kissed me and well I sorta asked him to.” Why doesn’t she looked shocked. 

“Took you long enough.” As she punched me in my arm. _Ow!_ Wait, what?? Guess she saw the shock on my face because she continued before I got a word out. “I’m just saying, I know you both wanted that for a while now. Give me every detail! How’d it happen? Was it hot??” 

“Um, copious amounts of alcohol.” Obviously.

Charlie rolled her eyes, “Details! You aren’t getting outta this one Winchester.” She poked me annoyingly. “And don’t say you don’t remember because you were drunk. That’s bullshit, you remember everything.” Has she always been this annoying?

“Fuck. Okay, I said it as a joke to fuck with Meg and Lisa. Cas attempted to call my bluff only I wasn’t joking. He said no, don’t look shocked. He said I was drunk and he isn’t an asshole.” 

“Cas isn’t an asshole? Ha!” She interrupted, which was nice because I had forgotten how to breathe for a second.

“Yeah, his words. Then I challenged him to do it and he did.” The last sentence was slightly rushed as the tears on my jeans suddenly became the most interesting thing in the room. Definitely _not_ Charlie’s face. 

“And… how was it?” Charlie had a wicked grin on her face like she already knew the answer to her own question. Fricken hate it when she does that.

“Fucking amazing Chuckles.” God damn that felt good to admit. All she did was hug me.

We talked for a few hours about everything, I even opened up about the night I realized I liked him and almost kissed a drunk Cas in Baby. Not going to say how many times I friggen blushed.

She dropped her deep _lesbian knowledge_ on me, telling me to get my head out of my ass and talk to Cas. At the very least tell him I _do_ in fact remember our mind blowing kiss. 

I just had to figure out _how._


	5. Chapter 5

**Summary for the Chapter:**

> Drunk Cas takes the next step!

I picked him up like normal on Monday, I was worried it would be awkward but it wasn’t. What exactly am I worried about? It’s Cas, my best friend. He did look handsome though, it was November and starting to get pretty damn cold in the mornings so he was wearing a long black trench coat. I decided to bring it up once Sam went on his way.

“So, Cas. It’s been a _few_ mornings and I still remember.” Was that smooth enough?

Cas smiled, his big gummy smile, the one reserved for certain people. “What exactly do you remember?” Still a dick.

“Fuck you, Cas.” We shared a laugh. Shit was still comfortable with him, I don’t know what I would do if shit got weird.

After a moment he leaned on baby, right next to me, our arms touching. “I remember too.” We were both smiling like fucking idots when the bell rung. He bumped me with his shoulder and went to walk to class but stopped right in front of me. I thought he was going to kiss me but he just said, “Until next time, Dean.”

Who said he was allowed to have a voice that fucking deep? And how could a voice wake up a dick? Goddammit. _Next time?_ He wants there to be a next time. Fuck… me too.

I stayed there for a bit, watching him go. Not just to watch him though, I couldn’t move my damn legs.

I was late to class.

I didn’t know when _next time_ would be but I really hoped it was soon. It wasn’t.

<<<<<<<<<<>>>>>>>>>>

Charlie was having a party during Thanksgiving break. I didn’t see Cas or talk to him much that whole week since we were both busy with family shit but I missed him. I couldn’t help but notice he had been a little less flirtatious with people at school, at least when I was around. It made me wonder if he was like that when I wasn’t around.

He showed up to Charlie’s house, hammered. Hammered to the point that Charlie made it a rule that _no one_ gave him anymore alcohol. He pouted but complied. I caught him watching me take a drink of my beer. His eyes were locked on my mouth as he licked his lips. Thankfully no one else noticed but when we finally locked eyes he raised his eyebrows at me with a smile. His hair was a disaster, his cheeks were flushed from the boose and he looked fucking delicious. No other way to describe it.

I saw him slip outside after that and followed. I told myself I missed him and just wanted to catch up. Truth is, I would have let Cas do whatever he wanted to me in that backyard.

He was standing in the left corner, out of the light, you wouldn’t know he was there unless you were looking for him. After a few seconds of self doubt I said fuck it and joined him.

“Hello Dean.” He had this shit eating grin on his face that made me roll my eyes.

“Hello Castiel.” Yeah, I didn’t sound nearly as hot as he did but whatever, two can play that game.

“Fancy meeting you here.” He stumbled forward. Shit, I forgot how fucked up he was.

“You good Cas? Need me to get you some water?” I wasn’t being a smartass, people always offered water to drunk people right?

He giggled. I say giggle because it wasn’t a normal laugh, it was a fucking giggle.

He stalked forward slowly, it kinda made me feel like prey and I kinda fucking liked it. My dick sure did. When he bit his lip my dick went from zero to sixty faster than my Impala.

“I am very thirsty Dean but not for water.” He was right in front of me at this point and I don’t know if it was the fact that we were in the dark or the fact that I had about nine beers in me but I was feeling bold.

“Drink up then Cas.”

I’ll spare the details on the sound I made when his mouth crashed into mine. But fuck.

Cas wasn’t holding back this time. I knew Cas was an aggressive kisser but _this_ was different. _This_ was raw and possessive, his tongue invaded every inch of my mouth as his hands roamed my body. He pulled back for a second to stare into my eyes, asking permission without words. He must have saw what he was looking for because he gripped my dick through my jeans. Again, not mentioning the sound that came out of me but it was manly, I assure you.

All I managed to say was a broken whispered “Cas…” before his mouth was back on mine.

I forgot where we were. I forgot we were in Charlie’s backyard with all of our friends inside. I forgot that I was straight. Nothing else mattered. I was so into the moment I didn’t feel exactly when the shift happened and his hand was inside my open jeans gripping my bare dick but holy shit. Cas had _big_ hands, I expected it to feel different than any chicks hands but I did _not_ expect it to feel so fucking good. His hand wrapped around my girth with ease and he knew exactly when to speed up and when to slow down, the dude was a fucking professional. When he whispered in my ear I almost fucking came, “No coming until you beg.” Goddammit.

For my ego, let’s say this went on for ten minutes.

Ten minutes later, I felt like I would explode. I had sucked a giant fucking hickey on his neck in that time and dug my hands into his shoulders so hard he would definitely have bruises. But he never faltered. “Dammit Cas, I need to come.” Again, manly.

“No, no sweetheart. Not yet.” He slowed down again, fuck. His goddamn voice was so deep.

I couldn’t take it anymore, if Cas said to beg, I was going to fucking beg. “Please Cas, please.”

Never repeat this asshats.

Cas laughed seductively, “Come for me Dean.” He didn’t need to tell me twice. I stifled my moan in his neck, blowing my load all over his hand and the grass below us. My body twitched as he stroked me through my orgasm.

I’ve had a lot of sex and a lot of orgasms, but that was mind blowing. No chick has ever told me when I could come or been able to hold me in place with strong hands. Cas was the most dominant person to ever touch me and I fucking loved it. Go figure the dude was a top. Did this make me a bottom? Shit.

Once the stars disappeared from my vision I realized my softening dick was still in Cas’ hand. We stared at each other for a moment before he let go. His dick was still _very_ hard so I reached for it without thinking, causing him to close his eyes and take a deep breath.

Now I know I would never be able to jack him off as good as he just did me. Even touching a dick from this angle was awkward since I’ve only ever touched mine. Cas asked me if I was sure.

Yes. Yes I was sure. I still am.

And I would have done it if Charlie didn’t burst outside to say the stupid pizza had arrived.

He faked a pout and took a step back. “Next time sweetheart.” Again with the next time and why did the word sweetheart give me the chills? It never has before.

I slapped his back before we walked inside and noticed he flinched, hard. The grunt he made sounded like I seriously hurt him. Just as I was going to ask what the hell happened Charlie was asking what we were doing out there. He slipped out of the room before I could get another chance. Probably to wash my come off his hand. The thought made me shudder.

My best friend just gave me a hand job in a backyard. And I loved every second of it. How did we get here?

When Cas came back out I was disappointed the bulge in his jeans was gone. I didn’t realize how bad I wanted to see his dick until tonight. It felt huge when I grabbed it through his pants but I had to know what was in there.

Charlie pulled me out of my thoughts when she yelled at Cas, “Cas what the fuck is that? You go to the bathroom for 5 minutes and managed to get laid? Who was even back there?” You could see her wheels turning as she looked around the room, trying to see who was missing, I was so thankful she was too drunk to actually put two and two together.

“I don’t remember his name Charles, I probably couldn’t pick his face out in a crowd but he had a beautiful dick.” I know the asshole saw my blush before I took a long drink out of my beer. When I looked back at him, in true Cas fashion, he was fucking smiling at me.


	6. Chapter 6

**Summary for the Chapter:**

> The boys have some fun in Baby

The flirting with Cas definitely went next level after that. I mean, there is a huge difference between Cas’ regular flirting and his _I’m going to fuck you one day flirting_.

I could go into details but I’d rather read you our text message thread the Tuesday after Charlie’s party. I’ll get right to the good stuff.

** _C- Nothing much, just sitting here thinking about that beautiful dick you have. You?_ **

How the fuck… why the fuck would he send that out of nowhere. I was sitting next to my DAD at the dinner table and he sends some shit like that! I dropped my phone into my plate of food and got bitched out. Dad threatened to take my phone away if I pulled it out again at the table. The last thing I need is for him to take my phone with _that_ fucking message thread open.

I completely lost my appetite. I picked at my food for a minute, feeling Sam’s eyes on me. My face always gave me away. Once we were excused I ran upstairs and slammed my door. It took me a second to even get enough courage to reread the message. He hadn’t texted again. What do I say?

** _ D- Dude! You can’t text shit like that without warning! I was at the dinner table. _ **

** _ C- What kind of warning would you like?  
C- In the future._ **

** _ D- I don’t know. Send the damn eggplant emoji or something._ **

** _ C- *eggplant emoji_ **

** _ D- Asshat. _ **

Now I don’t know if it was because it was text but I suddenly felt bold.

** _ D- I would say I’ve thought about yours too but I didn’t actually get to see it._ **

** _ C- Want to?_ **

I dropped my phone again. Shit. Is he about to send a dick pic? Does Cas send those?

** _D- Yeah…_ **

Fuck. I started pacing my room. When my phone vibrated again I jumped. Shit it was a picture. It took me a moment to open it. And when I did, it was a picture of an actual fucking eggplant.

** _D- You should see a doctor._ **

** _ C- I have. There’s nothing they can do._ **

I set my phone down to catch my breath. Why did I get so worked up over the idea of seeing Cas’ dick? Fuck I have issues. After a few minutes he text again.

** _C- Come over and see it._ **

Yup, you guessed it. I freaked. Charlie says I had a _full gay panic._

I didn’t respond for a bit and he didn’t pressure. Fuck I wanted to. But I didn’t think I should. Was I ready to actually have sex? Because if I went into Cas’ room, there was no way around it. I wanted it but I wasn’t sure if I was ready for that.

I was definitely ready to fuck around a little more tho and even more ready to actually see Cas’ dick. That fuck it part of my brain kicked in and before I realized I was in Baby driving over to Cas’ house. I took a deep breath and sent him a text.

** _D- Come outside._ **

** _ C- … _ **

Fuck, hurry up and respond Cas. When the three dots disappeared and he didn’t send a message I almost drove off. Was he just fucking with me again? Shit.

After a minute of nothing I glanced over at his house and he was walking up. My heart was literally pounding in my chest, was this how a heart attack felt? Has gay panic ever killed a man?

He climbed in the car with a grin. “Hello Dean.” He was wearing black sweatpants and a white shirt, he didn’t bother to put on a jacket and his hair was still wet from his shower.

“Hey Cas. Cold?” Good opener. Didn’t give much away. Voice hardly cracked. Going smooth so far.

“Why don’t you warm me up Dean?” Well shit. Did he make his voice deeper? Fuck.

“Uh… I...” I fucking stuttered. No words came out. Not smooth anymore, can I be any dumber?

Cas smiled, apparently enjoying this. It felt like I was under a microscope and it suddenly got really hot in the damn car. I could feel the panic rising in my chest until Cas suddenly put a hand on my leg. “Dean, are you ok?”

I scratched the back of my neck and barked out a laugh. No, not ok. “Of course Cas. A-Okay.” Convincing? Yeah... yeah it totally was.

“We won't do anything you don’t want to do. But if you are up for it…” Cas slid his hand closer to my dick, staring into my eyes. I couldn’t talk hell I couldn’t breathe. All I could do was nod. Glad it was enough.

He slid closer hesitantly, more hesitant than I’ve ever seen him be. “Relax Dean. I’m not going to do _anything_ until you relax.”

Dammit. How am I supposed to relax? The anticipation was killing me, I couldn’t relax and I damn sure couldn’t wait anymore so I kissed him. It started slow and unsure before Cas pulled me to the middle of the seat and straddled me in a matter of seconds. He slammed his mouth back into mine, erasing all my doubt.

Cas gripped my hair, pulling to expose my neck. Sucking a hickey while grinding his dick into mine. I could feel he was just as hard as me. I finally managed to get only one word out, “Backseat.”

He pulled away and looked at me, probably to gauge how serious I was before he hopped in the back. Once I climbed in the back with him he started unbuckling my jeans. I don’t know how I managed to remember to keep breathing at this point, I thought I would come the second his bare hand wrapped around my dick.

He stroked it a few times as he stared at me. I let my head fall back against the window as I watched him. Cas licked his lips and smiled at me before he lowered his head towards my crotch.

I’ve had a few blowjobs in my life, there's always that _excitement_ as a girl goes down on you, you know, before her mouth _actually_ touches your dick. The excitement from just knowing how good it’s about to feel, even if the girls never swallow, it’s still great to watch.

Once again, this was different. The excitement I felt as Cas lowered his head was out of this world. I embarrassingly almost came untouched at the sight. When his tongue touched it the first time I thought it was over. No fucking way I’d last long. I held my breath, hoping I could enjoy it for a bit before coming like some 8th grade virgin being touched for the first time.

I got my breathing under control after a moment, watching as Cas took his time tormenting me with his sinful mouth. He licked from the base to the tip, lapping up the precome that leaked out. He seemed to be thoroughly enjoying himself, which is not something you see often. Most chicks only suck you off because they feel they have to, I had _never_ received a blowjob where the girl seemed _this_ turned on while doing it.

But Cas… Cas was fucking loving it, and so was I. He sucked hungrily, moaning as I slid down his throat. He swallowed the entire length without gagging, I had to grip his hair to keep myself from flying the fuck away. The moan he made confirmed that Cas definitely likes his hair pulled so I didn’t let go.

Can we say ten minutes again? Let’s go with that.

About ten minutes later I couldn’t hold back anymore. “Cas. Gonna come.” I didn’t want it to end but I had to give the guy a warning. Except it didn’t end, he moaned in approval and kept going. He wasn’t going to stop. Holy shit, no way he was going to swallow. I had to watch, I couldn’t look away. He bobbed his head and slid all the way down again just as I came, straight down his throat. He still made no motions to pull off and sucked me through my entire orgasm, my hips bucked as he swallowed every drop.

I could have fallen asleep then and there. Never in my _life_ has a girl blew my mind with a blow job and no girl has _ever_ swallowed for me. Even Lisa was a spitter. When Cas slid off with a pop. He sat back and looked at me, pupils dilated from arousal as he licked his lips. His dick was tenting his sweatpants and I was tempted to return the favor. Except I had no fucking clue what I was doing.

“Ready to see it Dean?” Cas asked with a smile. I nodded, because apparently I don’t know words anymore. I may not know what I’m doing but Cas sure does and he has no trouble taking control.

Cas slid his hands into the waistband of his sweats and slowly slid them down, watching me intently. As soon as his dick sprung free I gasped. Yeah, it wasn’t my finest moment. But goddammit was Cas packing. He smiled at my shock and slowly grabbed his erection, staring at me while he stroked himself. It was fucking hot. I slowly made my way closer and just as I reached for his dick he moaned my name.

If I didn’t _just_ blow a load into Cas’ throat I would have jizzed my pants. His dick was smooth, I mean, probably not too different than mine but it felt different because it was very much _not_ mine. He was slightly wider than I was and definitely had an inch or two on me. And I’m not small by any means, let me just set that straight.

He coached me through it, told me when to squeeze and when to speed up, all while watching me through hooded eyes. I could feel when he was getting close, his breathing changed as his hands tightened into fists. Knowing he was close and that _I_ was the one getting him there was exhilarating. I suddenly wanted to be the _only_ person in the world to make Cas feel that way.

Cas gripped my hand and started fucking into it, snapping me out of my daze, making me want more of him. “Come for me Cas.” I didn’t realize I was saying it until the words were already out. It was all Cas needed though, he moaned my name and exploded into my hand, his hips shuddering to a stop as he collapsed back into the seat.

His eyes were closed and both of our spent cocks were just hanging out of our pants as we caught our breath. When he opened his eyes he laughed, “That was great, next time let’s go for a homerun.” Apparently my face made him laugh harder.

“Shut up Cas.” I pushed his shoulder but couldn’t help but join in his laugh. We cleaned up with some random napkins I found in the car and then he leaned in and kissed me again, no tongue, just a soft chaste kiss.

“I’ll be gentle, I promise.” He winked as he got out of the car. “See you tomorrow, Dean.”


	7. Chapter 7

**Summary for the Chapter:**

> Bathroom fun at school?

Well shit. Did that just happen? Did that just _actually_ fucking happen? 

I watched Cas go inside his house, unable to move. Holy shit, that was awesome! Just thinking about it had my dick back in the race. No time for that now, gotta get home and make up some lame excuse as to why I snuck out at 9:45pm on a school night. 

I told them Cas had my notes from class and I needed them back to study. They didn’t even question it, I had a whole speech planned that I didn't need. I’ll save it for a later date. 

After my shower I laid in bed unable to sleep. I kept picturing Cas’ mouth on my dick every time I closed my eyes. I already wanted no, _needed_ more of that. It was after midnight when I finally succumbed to my exhaustion. 

The drive to school was… _entertaining_. Sam let Cas have the front seat, which should have set off some red flags in my head but didn’t. I was too excited to be this close to Cas again, there was this electric current between us that felt like a live wire. He even positioned himself so he could face me better, both of us struggling to keep our hands to ourselves. 

“So, Dean. Who gave you that hickey?” What the fuck Sam! 

“Such a lucky _girl_.” Cas to the rescue. Hopefully Sam didn’t notice the hesitation before the word girl… I did. 

When I dared to glance at Sam in the rearview mirror he was looking out the window, smiling.

We didn’t really talk about it, which wasn’t surprising. What would we even say? Cas had this smirk when he looked at me though, he was definitely thinking about it too. 

Cas and I only had two classes together this year, second and fifth periods. We had lunch together too so we would always walk to fifth together. Unfortunately Meg was in this class as well so she never missed an opportunity to talk shit, especially if we were late. Today, we were very late.

Cas said he had to use the restroom so I followed, might as well take a piss before class too. But Cas had other plans in mind. 

We used the restroom like normal, there were other dudes in there but Cas still kept peeking at my junk with this stupid grin. I leaned over to whisper, “Take a picture it’ll last longer.” The look on his face was pure excitement, I had to clear that up. “It’s a joke Cas, you can’t have a picture of my dick.”

The look on his face changed, excitement was replaced with dominance in a matter of seconds. “I can’t?” He tilted his head as he walked to wash his hands, never taking his eyes off me. “Are you telling me no?” 

I washed my hands, not sure if I was more nervous or excited. When the last person left the bathroom I turned to meet his eyes, “Depends. What if I was?” Cas let excitement dance in his eyes for a second but before I could comment on it he had me pinned to the wall. 

He slowly reached between us and gripped my dick, which was fully awake at this point. Cas seemed to enjoy that. “Already Dean?” He moved his hand away and pushed his hard dick into mine. “Go in the stall.” I might have whimpered a little when he moved away from me but he didn’t have to tell me twice. 

I slid in the stall with him at my heels and was on him the second he locked the door. I completely forgot we were at school. In that moment, all I wanted was Cas. Then and there I realized I was ready to go all the way with him. I trusted Cas. 

It felt like a race as we unbuckled each other’s jeans. He won of course and dropped to his knees. Just the memory makes me shudder. Our location must have been in the back of Cas’ mind because he wasted no time sliding me down his throat. I gripped his hair knowing how much he loved that and he moaned, the vibrations traveling up my spine. I wasn’t going to last long, just as I felt the beginnings of my orgasm build someone walked in the bathroom. 

Neither of us moved. I looked down at Cas and he was looking straight up at me. I wish I had a picture of his lips spread over my cock and those angelic blue eyes staring into mine. His gaze never wavered as he slid his mouth off painfully slow. He stood up so we were eye level again and put his left hand over my mouth and gripped my dick. 

Covering my mouth was smart because whoever the fuck came in here was taking the longest piss ever and it muffled the moan that tried to escape. Cas stroked, keeping me pinned to the wall, until the other kid left the bathroom. He let go of my mouth to slide his jeans down, “Spit in my hand.” Gross but again, Cas didn’t have to tell me twice. 

He lined up our dicks and the second they touched we both moaned. Cas did all the work, I just stood there while the most beautiful dude on the planet rubbed his dick on mine. It didn’t take long before we were both getting close. I felt the only way I could contribute was to pull up our shirts and hope we didn’t come on them but it was hard to care in the moment. 

When Cas reached down with his left hand and slid a finger behind my balls I almost lost it. He didn’t go inside but he put pressure around the rim and I realized I wanted more. As soon as I pushed into his finger he smiled, “Oh baby you _are_ a beautiful bottom aren’t you, no coming yet sweetheart.” Goddammit Cas. I don’t know how he does this but the asshat was going to make me beg again. 

In any other circumstance I would have taken offense to the bottom comment but not here. If Cas said I was bottom I was fucking bottom. I used to think the bottoms were the chicks in the relationship but that doesn’t have anything to do with it. Cas takes control and I love it, I felt no shame... _in that moment_. 

“Cas. Come.” I couldn’t form words again but he knew what I meant. 

“Say please.” If you’re reading this Cas, you’re a dick for that.

“Fuck. You. Cas. Please.” Yeah I said it. Fuck off.

“Come with me.” Yes sir.

He sped up a little as his hips shuddered just as I came. I came so hard I literally went on my tiptoes. Cas followed seconds later, our come splattering both of our stomachs. 

As he slowed, rubbing us both through our come down he stared into my eyes. I couldn’t help it so I kissed him. This kiss was _different_, it made me feel like maybe Cas actually might love me too. Like maybe this was more than sex for him too.

“Cas, if you invite me over again, I’ll come up to your room.” I don’t know why I said it, but it made him happy. Glad he knew what I meant and I didn’t have to spell it out. Then again, that was one of the reasons I fell in love with him to begin with I guess.

“Are you sure Dean?” He asked, longing in his eyes.

“Yeah. I’m sure. You know we’re late as shit now right?” That snapped Cas out of his trance and he pulled away, making me regret that I said it. 

“Next time.” Once again. 

It was becoming my favorite phrase.


	8. Chapter 8

**Summary for the Chapter:**

> Dean is ready... or is he??

We decided to just skip English class that day. Once we were all clean we would have been almost thirty minutes late so we didn’t see the point. We stayed in the bathroom which probably wouldn’t look good if people saw us in there earlier but it was hard to care after orgasms like that.

It was nice just hanging and talking with my best friend, it felt like old times, when it was just us. Except it wasn’t like old times because I wanted to kiss him the entire time. Definitely didn’t used to feel that way. When we had about five minutes left I said fuck it and kissed him. I was hesitant at first but he was all for it.

We made out until the bell rang, just as both of our dicks started to wake up. Both of us left the bathroom with multiple hickies on our necks… how the _fuck_ do we explain this? When I saw him after school he had already been questioned by Charlie but the second she saw my neck I could tell that she put it together. Benny walked up at the perfect moment so she didn’t push the envelope, but I saw the knowing look on her face. It was easier just to avoid everyone’s eyes.

“Damn who marked you guys up?” Benny asked, completely clueless.

Cas answered first, “You’d be surprised how many homos are on the football team Benny.” How did he have an answer for _everything?_

I unfortunately don’t think as quickly, “Lisa. Uh... call it a moment of weakness. Never again Benny, never again.”

“Lisa wasn’t even here today and she came to do that? That girl must still love you.” Fuck. I didn’t even pay attention to whether Lisa was at school or not. I did the only thing a terrible liar like me could do, I kept my mouth shut and gave a noncommittal shrug.

Sam walked up which caused just enough of a distraction, at least until he saw my neck. “Damn Dean that’s like two more than you had this morning!” I saw Cas shift to stand so Sam couldn’t see his neck, to which I was grateful. I only left two on his neck and both were on the same side. The asshole put them on both sides of my neck so the conversation with my mom that evening was interesting. Just not as interesting as the conversation I had with Sam.

Sam walked in my room before I could shut the door, “What Sammy?” I think I somehow knew what was coming.

“Dean.” He had his concerned Dr. Phill face on. “How long has it been going on?”

“Spit it out Sammy.” When in doubt, be an asshole.

“You and Cas. How long?”

Let’s ignore how high my voice was when I responded. “What are you talking about?” Avoid or lie. Always been my motto.

“Dean, I don’t care. And you shouldn’t either. You guys seriously love each other, I can see it anytime you even _look_ in the other’s direction. Why not go for it Dean?”

Fucking asshat always made sense, even when I pretended he didn’t. I caved.

“It’s not that simple Sam.”

“Like hell it isn’t Dean. What’s so complicated?”

“Well for starters, I don’t think Dad would be very happy having a gay son.” It was my biggest fear.

Sam laughed, “Mom and dad wouldn’t care Dean, they love you. And they love Cas, they never cared that he was gay.”

“Cas isn’t their son Sam. It would be different. I have to go, I told Cas I would come over, don’t smile bitch.”

“Whatever jerk, your family loves you, stop being a pussy.” I watched him leave my room with my mouth open, did my baby brother just call _me_ a pussy?

Dean Winchester is no pussy, time to prove that.

** _D- You should invite me over Cas, right now._ **

** _ C- Dean, would you like to come over and fuck?_ **

** _ D- Smooth man._ **

** _ C- I mean watch Netflix… maybe chill._ **

** _ D- Be there in a few._ **

My confidence ended there. What the fuck was I thinking? Sam was right, maybe I am a pussy? To be fair, I’ve never done this before.

** _D- Sorry Cas, mom’s not too happy with my neck. Rain check?_ **

** _ C- I would apologize, but I have no regrets. Your rain check is good for two weeks. Use it wisely. _ **

<<<<<<<<<<>>>>>>>>>>

I was out of excuses. My rain check was about to expire and we really were running out of places to hide at school. Over those two weeks we fucked around in some way every single day. We couldn’t get enough of one another and Cas’ blowjobs were _out of this world_. I told him I was ready to try and return the gesture and he told me we would do that when I stayed over.

Cas made the decision the last day before Christmas break. “You’re staying the night, no getting away this time Winchester.” He winked before walking to his next class.

Shit.

That evening I told my parents I’d be staying over at Cas’ house and they didn’t think twice. I hardly ate dinner from nerves but if I’m being honest, I was more excited than anything. When I went upstairs to pack my bag, I had a text from Cas.

** _C- P.S. I’ll be gentle ;)_ **

** _ D- Kiss my ass_ **

** _ C- Oh I plan on it sweetheart, how else am I supposed to open up that beautiful virgin hole?_ **

Ok, so I did not expect that and even more, I did not expect my dick to wake up at the thought. Fucking traitor dick! I guess I took to long to respond because Cas texted again about 30 second later.

** _ C- Are you blushing Dean? Or did all the blood rush to your cock?_ **

**Sonofabitch I hate him... ok I don’t but he’s a dick.**

** _D- Blow me Cas_ **

** _ C- I plan on that too, we do have all night_ **

I had to give myself a pep talk to even get in the car. And don’t even get me started on the drive there. Pretty sure I was going 10 miles under the speed limit and I when I actually pictured Cas’ _giant_ dick I slammed on the breaks and almost got into an accident. Get it together Winchester! You are _not_ a pussy!

Cas was waiting outside with a smile. I don’t know how the dude can walk around with so much self confidence but he was borderlining cocky at this point.

“Lose the grin, Cas.”

“After you lose yours, Dean.”

We walked in and his whole family was in the living room, talk about awkward.

“Hey Dean, what’s new?” Cas’ dad Chuck asked and I hesitated in my response. Oh nothing much, just about to go upstairs and fuck your son. Or do I say _get fucked_ by your son? Either way, no big deal.

“Nothing much Mr. Novak.” I glanced at Cas and he hid a smile behind his hand. Jackass.

“Still dating... what was her name? Lauren was it?”

Ha, Lauren. “Nope. Living the bachelor life now.” Shut the fuck up Cas.

Cas’ mom passed away a few years ago and his dad has been really nice since. I feel bad for the guy. Dinner went ok, Cas sister Anna always flirted with me which used to be fun but Cas hated it. He kicked her under the table when she commented on me _filling out_ this summer. I got the urge to tell her I was more into her brother but lost the nerve. Those comments are more Cas’ thing.

His brother Michael was three years older than Cas and just an _asshole_. You know those jocks in the movies that you just wanna run over with your car? Yeah, that was Michael. Apparently he was home early for Christmas break and I could feel the tension between him and Cas.

Michael always made fun of Cas for being gay and picked on him for being the _baby_. I’m sure he’s pissed Cas is as tall as him now and doesn’t take his shit anymore.

It all felt normal, I almost forgot what we were about to do upstairs. _Almost._


	9. Chapter 9

**Summary for the Chapter:**

> THE SEX!!!

Anna asked if we wanted to watch a movie but Cas said no before I could respond. _Smart_, because I was about to say yes and stall. I felt like a dead man walking the entire trek up the stairs. When we walked in his room, I set my backpack down and turned to look at Cas, he was just leaning against his closed door, watching me. 

“You just gonna stand there and stare Cas?” I don’t know where that confidence came from but it was gone the second he started walking towards me, like a lion excited to devour a meal. A sexy lion if I’m being honest. 

Cas licked his lips and adjusted his already semi hard dick, which completely woke up mine. The second we were face to face he kissed me. The kiss was slow but possessive as he backed me into his wall. He unbuckled my pants without me even noticing and gripped my dick, sending a shiver up my spine. “You going to let me have that beautiful ass sweetheart?” He kissed his way down my neck, lifting up my shirt to kiss down my stomach. 

As he slowly pulled my pants down he looked up at me, “Y-yeah Cas. It’s yours.” 

Cas approved of that answer, the smile he had made me have to grip the wall for support. “Yes, Dean. _Mine._” 

The blowjob was short but still just as good. I could have finished that way I wasn’t actually excited for what was to come. When he pulled off he looked back up at me, “Take off your shoes and shirt Dean and then go to the bed.” I complied, shrugging off my shirt instantly and slipping off my shoes as he pulled my pants the rest of the way off. I slipped off my socks and walked to his bed, Cas watched me the entire time. 

I was completely _naked_, laying on Cas’ bed while he stood over me, completely _clothed_ and I’ve never been more turned on in my life. 

“So beautiful Dean. You listen so well.” Cas said with a smile as he slid off his shirt. His hair was a mess as usual and I couldn’t wait to pull it. I watched him undress, taking in his perfectly sculpted body. He unbuckled his pants painfully slow and slid them down, it might have just been my anxiety but his dick looked bigger as it tented his briefs. He slid those off and climbed on the bed, hovering over me. “I promise I’ll be gentle, do you trust me?” With my fucking life Cas. 

“Uh huh.” Words aren’t my thing. 

He kissed me for a moment before reaching over for his bottle of lube, the sight made me gulp. We already had the whole, _“you’re clean right?”_ speech, so I was mentally prepared that Cas wanted to go raw… or as mentally prepared as I could be. We both got tested at the free clinic last month and haven’t been with anyone else. 

While he reached over to grab the lube, I noticed the corner of a tattoo on his back, “Is that a tattoo Cas??” I wonder why he didn’t tell me. 

“Yes. Want to see it?” He climbed off the bed and turned around, I gasped and sat up to get a closer look. Giant obsidian angel wings covered his entire back, the artwork was beautiful. They fit Cas’ angelic blue eyes perfectly. Cas was an angel. A sexy dominant angel but still.

“It’s beautiful Cas.” I ran a finger down his back, tracing the dark feathers. They had so much detail I felt like I could feel actual plumage instead of skin. 

“Thank you. You’re beautiful.” He turned back around to look into my eyes.

Cas set the lube aside and then climbed back on the bed, he began kissing me again and rubbing our dicks together softly. When he started kissing down my neck, my toes curled. Cas really knew what he was doing and he was doing everything to keep me calm and in the moment. He kissed down my torso and then lapped at my dick lightly, before he spoke, “I’m going to use my tongue first Dean, I’ll go slow but you need to stay relaxed ok. Remember sweetheart, you have to trust me.” 

He spoke so softly, so sensually, that all my doubts wavered. I realized then that I completely trusted him. “I trust you Cas.” 

He smiled and then slowly lifted my legs up. “We’re going to flip over in a little bit, but I know this is more comfortable for you to start.” He sucked me off for a few minutes before sliding off and gliding his tongue down the shaft to my balls. He didn’t hang out their long, my breath hitched as he made it to the hole.

I didn’t expect to love it, I thought _maybe_ it might feel sorta good. But goddammit Cas’ tongue was magic, he had to get up and put music on to cover up my moans. He worked me open for a good five minutes before he had me turn around and lean forward on a pillow. I had a moment of panic, I felt vulnerable as hell until his tongue returned to my ass, a little more aggressively this time. After a few minutes he reached around to stroke me, his strokes matching his tongue. I almost came. And I would have if he didn’t back out.

“You’re ready for more now sweetheart.” I heard the lube top pop open and freaked again. Cas felt it, he put a reassuring hand on my thigh and rubbed it. “I’ve got you.” 

I don’t know how or why his voice calms me so much, but it does. When he inserted a finger I embarrassingly jumped forward, but he was patient, he started rubbing me again to help calm my nerves. 

“How many fingers is that Cas?” 

Cas huffed a laugh, “Dean, that is one and it’s just passed my nail. I’ll go slower.” 

“No, no. I’m good. I can handle it Cas, keep going.” I could hear his smile when he spoke.

“Beautiful, just beautiful.” He began to move his finger, it wasn’t long before I was rocking back into him. He added another finger and again, waited until I was ready to move. I couldn’t imagine doing this with anyone else, but Cas had to be the most patient person I’ve ever been with. With every movement and every addition he went _my_ speed. Letting me have _full_ control, which is crazy since he was the one three fingers deep inside me. 

I wanted more, I wanted to give him more. “Cas, more. I want you, I’m ready.” 

He stopped moving his fingers and slid them out slowly. “You feel ready. There will still be an adjustment period but I won't move until you tell me ok? I’m going to put some more lube.”

I heard the cap again and a couple seconds later I felt him line up at the entrance. Ok, I panicked a little here. He rubbed my hip and waited me out. “Ok, Cas.” My voice shook a little.

Cas pushed in slowly, rubbing my hips the entire time. He stopped once the head was in I heard him moan lightly. Fuck, that had to be my favorite sound. I couldn’t help it so I pushed back a little more, just wanting to hear him moan again. “Shit Dean. Slower, I don’t want to hurt you.” He couldn’t hide the pleasure in his voice. I didn’t want to stop, hearing Cas’ moan made me want him even more. I wanted to make Cas come as hard as he had made me come the last few weeks, however I didn’t want to get hurt either and have to stop so I listened and let Cas take control.

After a few moments he bottomed out causing both of us to groan. Cas didn’t move for a bit, just allowing me to adjust and stretch around his ridiculous size. He gripped my shoulder and pulled me up so his stomach was flush against my back. It caused another stretch but it felt nice to feel his skin and hear his whispered praise in my ear as he kissed my neck. “So perfect Dean, you feel so fucking good.” He moved his hips in a small circle, not thrusting yet. “This ass is mine, Dean.” He grabbed my face to pull me into a sloppy kiss. 

“All yours Cas. I’m ready.” He kissed the side of my face as he slid out and thrusted back in. It hurt but not in a bad way. The stretch was pleasurable and I felt so fucking full, I loved it. So much more than I ever imagined. Cas bent me back over to lean on my elbows and then started fucking me. It didn’t take long for me to push back into him.

“Fuck Dean, you have me close already.” Cas moved his hips slightly to hit that _spot._

That fucking _spot_. I saw stars. No way his family didn’t hear me yell his name. I forgot they existed. 

“Fuck. Cas. Right there. Gonna come.” I felt it already, this orgasm was different than any orgasm of my life. Cas reached around and gripped my leaking dick, letting his thrusts move my body so I was fucking his hand. It took about six of those thrusts to have me exploding into his hand and all over his bed. Cas followed seconds later, moaning my name. I felt him spill into me, filling me up. 

Cas leaned forward and kissed my back softly. “You did so good baby. Fuck, I want this every day Dean.” 

It felt so good to hear that, even if it was just his euphoria talking. I whimpered when he pulled out, missing his skin against mine. He cleaned me off and then we cuddled. Which isn’t something I do often, but it felt so right. 

We tried a _couple_ things that night. Cas walked me through my first blowjob and it was harder than I anticipated but I swallowed. _Ungracefully_ but that isn’t the point, I’m no quitter. We hardly slept, my balls felt empty the next morning and my ass was sore but it was the best sex of my life. 

Breakfast wasn’t as awkward as I thought it would be. Chuck made pancakes and Anna kept looking at me, she might have heard. I’ll have to ask Cas later. Cas walked me to my car and climbed in to say a proper goodbye. We made out for a bit before he got out. He leaned in the window and winked, “Miss you already Dean.” 

He walked away after that and I watched him go inside before I said anything, “Miss you too Cas.” And I did.


	10. Chapter 10

**Summary for the Chapter:**

> Insert Dean’s gay panic...

Well shit. I finally had sex with Cas. Where do I even begin? It was everything I hoped for and more. I loved every single second of it and it can _never_ happen again. Ever.

Let me explain, I _can’t_ be gay. I just fucking can’t! How am I supposed to explain this to my dad? _Hey pops, cars running great. Oh, by the way I’m gay as shit. See ya later._ Fuck! _Wait, not only am I gay as shit, I’m the fucking receiver. Your eldest son just got ass rammed into Cas’ mattress and loved it. Good talk_. Goddammit. 

Nope. Not happening.

Thank god Christmas break started and I was able to fake the flu and stay home. Now I just have to avoid everyone, for eternity. 

Cas can have anyone he wants. He won't give a shit. 

I mean, he texted me a few times at the beginning of break but gave up after a few days. Just like I thought, he’s fine. Cas is probably out fucking someone else right now. I don’t even care anymore. And you know what’s even better? I don’t care, that I don’t care. 

Charlie wouldn’t let it go though and barged in my room _again_. Dammit mom, I’m gonna have to have a talk with her about boundaries. 

“What the _shit_ Dean!? You can’t just fall off the face of the earth and not expect your friends to freak. What happened?” She stood over me with her arms crossed. I wasn’t sure if Cas spoke to her but he didn’t, he didn’t tell anyone.

“Dammit Charlie, I just want to be alone right now.” I tried to block my face with a blanket and she ripped it off. 

“No. Stop pushing everyone away! Something happened with Cas huh? Just talk to me Dean.” She looked genuinely worried.

I cried. Fucking face leaking everywhere like a middle school teenie bopper.

She just sat there. She didn’t try to talk or pressure or even rush me. She was just there and it was exactly what I needed.

“I can’t do it Charlie. I can’t be gay.” She hugged me after that, even cried with me a little. Guess she remembered how this felt.

I told her about everything. How Cas and I have been fucking around the past two months. The fact that we finally went all the way and it was the best sex of my life. How I’m in love with him. 

Up until this moment, I hadn’t said those words out loud. Yeah, a couple people knew I had a crush on Cas but the L word? Nah, Dean Winchester doesn’t _do_ love. Right?

Except I did. I fucking loved the guy. To the point where I wanted to bring him home for Christmas and be like suck it dad, this is me. I’m a gay… 

But don’t suck it literally. Not like that. Ugh.

Anyway, I just couldn’t. If I wasn’t Dean friggen Winchester, ladies man of Lawrence High, who the _fuck_ was I? 

Right before Charlie left, she told me I've been worrying about all the wrong things. Things that don’t matter. If I actually loved Cas, nothing should hold me back. Especially when he loves me too. She’s probably right, but I couldn’t help but doubt the guy loved me back. 

So it didn’t change anything. What would I even say to Cas? Sorry I freaked out and cut you off... 

I guess that would be a start actually. 

He texted again, the morning we were supposed to go back to school. I actually was sick this time so I talked my parents into letting me stay home one more day. I planned on texting him to let him know but he texted me first, _Got a ride. See you at school_. I didn’t respond of course. 

Cas didn’t even want to ride to school together anymore. How the fuck did we get here? 

I went to school the next day. Couldn’t hide in my room forever. 

Did I mention Cas and I had second period together? _Awkward._

I managed to not see him at all until then and when class started, he came running in right after the bell. Giving us _no_ chance to talk. He looked cute as hell in this hooded leather jacket I’ve never seen him wear before, black jeans and some black biker boots. When he slid off his hood his hair was sticking up in every direction and god dammit I wanted to run my hand through it. 

He plopped his ass in the seat next to me like nothing and threw me a tight smile. 

I couldn’t help but glance at him every five minutes and I still had no clue what I even wanted to say. He only caught me looking once, I looked away as fast as possible and felt his eyes on me for awhile. After class he stood up to leave and I finally grabbed his arm, “Wait, Cas.” I looked around the room as more people left. Wishing we had privacy.

Cas scoffed at me, “Don’t worry about it Dean, I can take a hint.” 

Then he left.


	11. Chapter 11

I did _not_ expect that at all. He seemed genuinely hurt and it made me feel like shit. A couple weeks ago it felt like we were together, actually _together_ and now he could hardly look at me. Not that I can blame anyone but myself. 

Truth is, I’ve had a lot of time to think and I am finally ready for more. More of Cas and what we might become. Ready to make him mine. 

The way he looked at me that day… Cas has always been good about speaking without words, using those beautiful eyes to get his point across. _That day_, he told me I broke his heart. I never want to see that look on his face again and I definitely don’t want to be the cause. 

I couldn’t focus on anything else, all I could think about was Cas’ hurt cerulean eyes staring into mine. It suddenly became clear what I had to do, I had to get him back somehow. I wasn’t sure exactly how to go about it or what to say so I decided to improvise. Cas would see through any bullshit anyway. 

I knew he had art class third period so I lied to get out of class early so I could wait for him. He was one of the first to walk out which caused me to hesitate. “Hey,” I touched his arm as he walked by and he flinched. I couldn’t believe it, Cas _flinched_ when I touched him. It hurt, but I had no right to be upset, this is _my_ fault. “You got a minute? Look I’m-”

“Save it Dean.” He turned to walk away. 

“Cas come on. Let me explain.” I grabbed his arm again and he turned around and stepped into my space, backing me into the wall. I looked around nervously to see if anyone was paying attention. He leaned in as if he might kiss me… I turned away. 

Dammit.

Cas laughed bitterly and stepped back. “That’s what I thought. I hoped you had finally gotten past your bullshit fears or at least stopped caring so much about what everyone _else_ thinks of you. Guess I was wrong. I wont be your gay experiment anymore Dean. Step up or back off.” 

“Shut up Cas. You know you mean more than that.”

“Do I? Do I Dean? How the fuck would I know that? We’re _bros_ at school and then you text me when you want to try something new. And what happens when you _decide_ you’re _“straight”_ again huh? _I’m_ the regret you push aside. Fuck that. You’re a coward.” Cas walked away before I could speak or even fucking breathe. A coward?

When _did_ I start being a coward? I let the fear of the unknown hold me back my entire life. Shit, Dean Winchester _is_ a coward. 

Fuck that. 

Not anymore. 

It only took a minute for me to decide what to do and I knew exactly where Cas was. When I walked up to our friends normal hangout spot they were all there. Benny and Andrea were cuddled up together, Charlie and Cas were standing next to them talking, even Sam and his best friend Kevin were there. No backing out now.

Cas spotted me first, his face unreadable. Charlie turned to see what he was staring at, “Hey Dean, we’re having a debate. What-”

She must have stopped talking from the shock or maybe I just couldn’t hear her anymore because I instantly walked up and pulled Cas into a kiss by his shirt. He didn’t flinch or pull away, he kissed me back. _Fuck_ it felt so right. Before I knew it, we were full on making out in front of everyone. I faintly heard Charlie yell, “Finally!” 

When we finally broke apart Cas was smiling. Okay fine, I was too.

Benny spoke first, “Well damn Dean” Cas was still grinning but didn’t speak. 

“Shut it Benny. You suck face with Andrea all damn day and we all stay quiet, let me suck face with my boyfriend.”

Cas tilted his head. “_Boyfriend?_ It took you long enough, Winchester.” He was right. It really _did_ take me long enough.

“Shut the hell up and kiss me Novak.” Or course, he did and I could tell he was trying to push it too, pushing to see if I would break and make a run for it. He gripped the back of my jeans and pulled me closer. Two can play that game Cas. I ran my fingers through his hair and pulled, causing him to moan.

“Ok seriously, we got it. Get a room now guys.” Charlie made a gagging noise.

Cas pulled away, not because of Charlie but because we needed to breathe. He looked behind me and muttered “Shit.” I turned to look at what he saw and yup, you guessed it, Meg and Lisa were staring with their mouths hanging open. 

Cas laughed which caused me to laugh. Meg had a look of disgust and Lisa actually turned away crying. I almost felt guilty before realizing I have nothing to feel guilty about. 

“Damn, maybe you shouldn’t have fucked around with her recently, the girl clearly still has feelings.” Cas and I looked at each other and laughed. Benny was clueless.

“Yeah Benny, those marks weren’t from Lisa, that was Cas.” We could see the when the lightbulb went off in Benny’s head. 

“Shit Cher, you two been fucking around for months huh?” He looked over at Andrea and she laughed.

“Even I could tell babe.” I couldn't help but blush, guess everyone _did_ know already, well everyone but Benny. 

Turns out, Cas and I were just as disgusting as Benny and Andrea, we couldn’t keep our hands off one another. Charlie had the nerve to tease us for being so _gay_. It felt so damn good to be out. Well... mostly out. 

It was time to tell my parents.

I’m actually going to save the coming out details since I cried the whole time. In fact, my entire family cried. My mom said she knew, which was shocking. Guess it was something about how Cas and I looked at one another. My dad actually asked to be excused, which scared the shit out of me but he came back a few moments later with tears in his eyes, saying he didn’t care, that he loved me regardless. Which made the rest of us cry, we were like four babies at the dining table. Sam said he was proud of me, which felt really good. It all felt so fucking good. 

I didn’t have to live in the closet to be loved by my family. 

I was free.

I went to see Cas after that, his presence always calmed me but I had something I needed to say to him. He came out to my car, we almost got carried away with the making out so I had to pull away. 

“Are you okay Dean?”

“No. Well yes. I mean, I have something I need to say.” I stared into his eyes as he nodded, returning my gaze intently. 

“I never thought I’d find anyone who cared about me, who would be there for me through all the crap. But at some point Cas, I realized that… I realized it was you. You were right there in front of my face. I’m sorry it took so long and I’ve been a dumbass but I love you Cas.”

Cas smiled my favorite smile in the world. “About damn time.” He leaned into kiss me softly and then leaned back to look into my eyes again. “I love you too.” 

Awesome.

**Notes for the Chapter:**

> Thanks so much for reading! I decided to do a Cas POV so stay tuned!


	12. About Damn Time

**Summary for the Chapter:**

> Wait what do you mean Dean wrote a story about me? Can I see it? Fine, how about you let me tell you a story about a clueless boy named Dean Winchester. When I say clueless, I mean Narnia in the closet clueless.

**Castiel**

Let me start by telling you about the day I knew Dean was gay.

We were in the 7th grade. And Dean had made out with this very beautiful _very_ shallow girl named Bela. I had already kissed multiple boys and girls at this time but Dean hadn’t. He walked up to me with a fake smile, _I_ knew it was fake because I could always read Dean like a book. _Always._

Anyways, he walked up with his _dude mask_ on talking as though it was no big deal. But it was, and I could see that it was. I could also see that he didn’t enjoy it or at the very least was let down by it. He had a crush on Bela for months so I couldn’t understand why he was so disappointed. I filed that for a later time.

That same day, he walked up on me while I was making out with with some kid… I actually can’t remember his name… oh well. So, Dean walked up and just stood there. I knew he was there but to this day he doesn’t know I knew, did that make sense?

Anyway, he just stood there. Deer in the headlights, jaw open, the whole nine yards. He didn’t say anything and he damn sure didn’t look away. Not only did he not look away, he was _into it_. To the point that he popped a boner and took off running to the bathroom. Neither of us ever brought it up.

But my brain pulled that file from earlier and connected the dots. Dean wanted to kiss a boy. Kissing Bela wasn’t what he wanted because he wanted to kiss _me_. God don’t get me started on the fantasies that followed that awakening.

I definitely started flirting with him every day and I could tell he liked it but it also pushed him into the arms of like every girl around. You know, to convince himself he was straight.

Middle school hormones are no joke. Dean was making out with every chick he could get his hands on and I was doing the same, with boys. 8th grade was just a blur of groping and dry humping… okay maybe most of 9th grade too but 9th grade was when I got my first blowjob. I’m getting off track, this is supposed to be about Dean. But he did really _hate_ the kid that blew me. At this point, Dean was so far in the closet he had mothballs in his hair. He acted like my gay stories would turn him gay.

He’d say shit like, “Dude, I don’t want to hear that.” But not until I finished the story, of course. I also got my first girlfriend in the 9th grade. Dean got one, she had a friend, I was pressured.

If I’m being honest, it wasn’t horrible. April was nice most of the time but she was very jealous and possessive. It was probably worse because she knew I liked boys and girls.

You see, I don’t have some cool coming out story. I was just never _in_. I knew what I liked at a young age and I never kept it a secret. So, April was insecure with everyone I spoke to. It was annoying but we stayed together for about 6 months and lost our virginities to one another not too long after Dean and Cassie started having sex.

I can’t speak for Dean here but I really wish we didn’t waste so much time fucking around with girls when we could have been fucking each other. I know _I_ wanted to. I didn’t push it with him back then, I figured he would come around when he was ready and when he didn’t, well. I had a little fun, especially after I broke up with April.

When my mom died, Dean was there. More than anyone. I mean we already had this profound bond that no one compared to, but the second I texted him about my mom he ran over to my house. This was the summer before 10th grade, before the Impala days. He ran over, my dad let him up to my room and he just walked up and hugged me. I don’t know if I ever told him how much that hug meant to me. If it was anyone else I would have asked them to leave, I wasn’t in a good place. But it wasn’t just anyone, it was Dean.

Next to my mom walking in and hugging me, it was the next best thing. I cried in his arms for about 40 minutes and then we never spoke about it again. You know, guy code. Insert eye roll.

After that, my crush was back, hardcore. I should be ashamed about the number of green eyed dudes I fucked around with just to pretend it was Dean.

My first time with a guy was a drunken mess. A very fun drunken mess, in the school locker room. Turns out, the golden boy, quarterback of Lawrence was a whiny bottom. Dean was _not_ happy about this.

At first he didn’t believe me so _naturally_, he wanted every detail. It was for research though, not his spank bank, so he says. I know the truth now though, he definitely wanted to be the one I bent over in the locker room, _not_ Gordon. I made that up to him before senior year ended.

I’m getting off track, sorry I had an energy drink. So, Dean teased about the quarterback hiding in the closet... Right?!? Hypocrisy. Anyway. He saw Gordon flirting with Andrea a couple days later and told Benny about it. He knew Benny would flip! He had been pining over her since the first day of freshman year. So, Benny goes to practice pissed and hits Gordon during a play. I don’t know football, don’t quote me here. Benny was supposed to tap him some way and instead he laid him out. Gordon jumped up and hit him and they fist fought and got suspended. You should have seen Dean’s face when he saw Benny gave Gordon a black eye.

Dean didn’t want me with anyone else and I honestly felt the same but instead of talking about it we did what guys always do, avoid. Or just talk about literally _anything_ else.

This sadly went on for a couple years.

By junior year we had to outsource our sexcapades, between the both of us we had slept with most of our school so we were out of options unless we wanted a relationship.

Outsourcing was a challenge, there was no steady stream of ass for either of us so we caved and got girlfriends.

Meg was a bitch, not going to lie. She would always make comments on how Dean wanted her man, making him uncomfortable as shit. The longer our relationship went on the less I was interested in having sex with her. Nothing against her, she just didn’t have a dick. I started realizing I was more gay than bi before summer even started that year but I hung around a bit longer, purely out of laziness. Dean was less and less interested in Lisa too, we all could see it.

When we went to the beach at the beginning of summer, he was already mentally checked out of that relationship. I got a _little_ drunk and said things I probably didn’t need to say, but it didn’t scare him away. I actually almost kissed him that day but instead distracted myself with more alcohol. Mistakes were made. I woke up in the backseat of his car wondering how I got there.

He broke up with Lisa and instantly started flirting back with me. He even tried holding my hand a few times but that was one thing I couldn’t mess around with. Hand holding for me meant love. Did I love Dean, yes. But we weren’t a couple or anything near it so I didn’t want to put myself through that. I never even held Meg’s hand because I didn’t love her. I’m sure this sounds weird, so let me spell it out. Hand holding is more intimate to me than sex, call me crazy, it’s just how I feel.

When school started, he seemed genuinely jealous of my flirting. I can’t help it, I’m a flirt and if he wasn’t going to take the next step then I was at least going to have some fun this year.

When he found out about my one night stand at my family reunion… okay, that sounds _so wrong_. Let me clarify, my cousin brought her gay bff and we hit it off. He was a twink so it definitely wasn’t about to go anywhere but the sex was fun. Anyway, I saw the look in Dean’s eyes when he gripped the steering wheel. He was _not_ happy, but of course, he played it off.

I again _almost_ kissed him on my birthday and yeah, we were all wasted. Charlie made us play truth or dare and then dared me to kiss anyone in the circle. Dean’s eyes met mine and he looked terrified so I stood up and stared everyone down to torment them. That part was actually fun. I picked Charlie since the whole thing was her fault and she’s so gay, I knew she would be pissed. She screamed as I jumped on her and her dare backfired, it was amazing.

Speaking of kissing, let me tell you about _our_ first kiss. When Dean suggested we kiss to make Meg and Lisa jealous I was momentarily caught off guard, then I remembered how drunk we were. Of course I decided to mess with him, only to learn he was _not joking_. Fuck it was so hot. It took everything to pull away and not turn him around and fuck him against that minivan.

Once again, the fantasies of Dean took over my life. I _needed_ to kiss him again!

Charlie’s party was a blur for me. I completely forgot about it and got drunk at home with Anna in my room watching _Harry Potter_. When Charlie called me, yelling for missing her party, I rushed over. That walk was hell, I fell at least twice. I honestly don’t remember arriving at her house but I do remember the moment I saw Dean. I had to go outside to calm the raging hard on I got watching his lips curl around is long neck beer. I did _not_ expect him to follow me.

I remember the hand job clearly, more clearly than any other moment that night. My subconscious could never forget that beautiful cock. Don’t laugh at my shudder, I still can’t get enough. But I remember waking up the next day so fucking hard I had to rub one out just to stand.

Fucking Dean became number one on my to do list.

When I asked him to come over a couple days after Charlie’s party I was shocked he _actually_ came. As soon as he texted _Come Outside_ I almost jizzed my sweatpants. I walked out instantly, not bothering to grab a coat, I made up my mind that I was at the _very least_ sucking Dean Winchester off tonight. I was fucking _giddy_, no other word to describe it.

Our first time actually fucking… I have no words.

The best sex of my life, hands down. All I knew was, I wanted that ass every day, for the rest of my life.

The entire night was perfect, I had been wanting to show him my tattoo since I first got the outline done but I decided not to show anyone, not until it was finished. I also wanted Dean to be the first to see it. The wings are for my mom. I may not be religious but the thought of her being my guardian angel is comforting in its own way but enough about that.

When Dean shut down, it fucking hurt. Yes, I’ve had my share of one night stands but that was never Dean. I never wanted it to be Dean. He may have just been figuring this _thing_ out but _I_ knew, I was in love with Dean for years. To finally have that opportunity was a dream come true. I fucked him raw because I loved and trusted him. It was my first time without a rubber, in my entire life. Maybe Dean didn’t understand at the time but the things I did with him, I don’t just do with random hookups. I wanted to be _with_ Dean, I wanted to hold his hand.

I shouldn’t have pushed him but let’s all be honest here, Dean wasn’t about to step up to the plate without a little push.

I could have cried when he kissed me that day in front of everyone. It didn’t feel real, it was finally _our_ time.

When I told my family no one was surprised. Michael made fun of us but who cares what he thinks. Anna said she called it years ago but I’m sure that was just what she told herself to make herself feel better since Dean never gave her the time of day. Dad was kind of awkward, he asked if he should make me keep the door open when Dean came over. I responded with a “Why it isn’t like either of us can get pregnant.” Making him shudder and change the subject.

Dean’s family was just as welcoming as always but they enforced the _open door_ rule. I told Dean what he should say and he said fuck no. Guess it would take him some time to talk so freely about our sex, which is understandable. I didn’t push. It didn’t stop our sexcapades in the slightest.

It was worse when we finally graduated and moved in together. We both got jobs at the Dean’s Uncle Bobby’s Auto Shop. Dean did the car stuff, I just worked the counter. But we got to see each other a lot. Bobby yelled at us one time for flirting so we kept that to a minimum, he threatened to schedule us apart if we didn’t cut the shit. The sexual tension was amazing, leading to back arching orgasms the moment we got home.

I finally tried bottom after we lived together for a few months. I was fucking nervous but Dean was amazing. He was definitely the one I was waiting for.

Gotta go, Dean’s calling. The man is insatiable.

**Notes for the Chapter:**

> Hope everyone enjoyed Cas' side. 
> 
> (This was it's own one shot but I realized hardly anyone was seeing it so I think it is better off here)


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